PREPARATION OF OPTICALLY-ACTIVE AZOPHENOLIC CROWN-ETHERS CONTAINING 1-PHENYLETHANE-1,2-DIOL AND 2,4-DIMETHYL-3-OXAPENTANE-1,5-DIOL AS A CHIRAL SUBUNIT - TEMPERATURE-DEPENDENT ENANTIOMER SELECTIVITY IN THE COMPLEXATION WITH CHIRAL AMINES
K. Ogasahara et al., PREPARATION OF OPTICALLY-ACTIVE AZOPHENOLIC CROWN-ETHERS CONTAINING 1-PHENYLETHANE-1,2-DIOL AND 2,4-DIMETHYL-3-OXAPENTANE-1,5-DIOL AS A CHIRAL SUBUNIT - TEMPERATURE-DEPENDENT ENANTIOMER SELECTIVITY IN THE COMPLEXATION WITH CHIRAL AMINES, Journal of the Chemical Society. Perkin transactions. I, (21), 1997, pp. 3227-3236
With (2S,4S)-2,4-dimethyl-3-oxapentane-1,5-diol and (S)- or (R)-1-phen
ylethane-1,2-diol as chiral subunits, optically active azophenolic cro
wn ethers (S,S,S,S)-1, (R,S,S,)-2 (S,S,S,S)-3 and (R,S,S,R)-4 possessi
ng two phenyl and two methyl substituents together with the p-(2,4-din
itrophenylazo)phenol moiety have been prepared in enantiomerically pur
e forms, Temperature-dependent enantiomer selectivity in the complexat
ion of these crown ethers with chiral amines has been studied by the U
V-visible spectroscopic method in chloroform and from the observed ass
ociation constants, thermodynamic parameters for the complexation have
been calculated.